(6R,7R)-7-{2-{(Z)-2-[Acetyl-(4-methoxy-benzyloxy)-amino]-ethoxyimino}-2-[2-(trityl-amino)-thiazol-4-yl]-acetylamino}-3-chloromethyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 4-methoxy-benzyl ester

Base Information

• Chemical Name: (6R,7R)-7-{2-{(Z)-2-[Acetyl-(4-methoxy-benzyloxy)-amino]-ethoxyimino}-2-[2-(trityl-amino)-thiazol-4-yl]-acetylamino}-3-chloromethyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 4-methoxy-benzyl ester
• CAS No.: 182068-65-1
• Molecular Formula: C₅₂H₄₉ClN₆O₉S₂
• Molecular Weight: 1001.58

Synonyms:

Chemical Property of (6R,7R)-7-{2-{(Z)-2-[Acetyl-(4-methoxy-benzyloxy)-amino]-ethoxyimino}-2-[2-(trityl-amino)-thiazol-4-yl]-acetylamino}-3-chloromethyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 4-methoxy-benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of (6R,7R)-7-{2-{(Z)-2-[Acetyl-(4-methoxy-benzyloxy)-amino]-ethoxyimino}-2-[2-(trityl-amino)-thiazol-4-yl]-acetylamino}-3-chloromethyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 4-methoxy-benzyl ester

There total 9 articles about (6R,7R)-7-{2-{(Z)-2-[Acetyl-(4-methoxy-benzyloxy)-amino]-ethoxyimino}-2-[2-(trityl-amino)-thiazol-4-yl]-acetylamino}-3-chloromethyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 4-methoxy-benzyl ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

N-(4-methoxybenzyloxy)phthalimide (2014-61-1) → (6R,7R)-7-{2-{(Z)-2-[Acetyl-(4-methoxy-benzyloxy)-amino]-ethoxyimino}-2-[2-(trityl-amino)-thiazol-4-yl]-acetylamino}-3-chloromethyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 4-methoxy-benzyl ester (182068-65-1)

Guidance literature:

Multi-step reaction with 8 steps

1: 1.)H₂NNH₂*H₂O, 2.) HCl / 1.) MeOH, room temperature, 10 h, 2.) MeOH, room temperature, 1 h

2: 95 percent / Et₃N / tetrahydrofuran; H₂O / 1.5 h / Ambient temperature

3: 52 percent / NaH / dimethylformamide / 15 h / 0 - 10 °C

4: 85 percent / HCl / ethyl acetate / 10 h / 0 deg C - room temperature

5: 98 percent / Et₃N / CH₂Cl₂ / 1.5 h / 0 deg C - room temperature

6: 100 percent / H₂NNH₂*H₂O / methanol / 14 h / Ambient temperature

7: 78 percent / ethanol; CHCl₃ / 10 h / Ambient temperature

8: 1.) Et₂NH, 2,6-lutidine, 2.) POCl₃ / 1.) CH₂Cl₂, -30 deg C, 0.5 h, 2.) CH₂Cl₂, -30 deg C - (-15) deg C, 4 h

With 2,6-dimethylpyridine; hydrogenchloride; sodium hydride; hydrazine hydrate; diethylamine; triethylamine; trichlorophosphate; In tetrahydrofuran; methanol; ethanol; dichloromethane; chloroform; water; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1016/0960-894X(96)00381-2

Reference yield:

p-methoxybenzyl chloride (824-94-2) → (6R,7R)-7-{2-{(Z)-2-[Acetyl-(4-methoxy-benzyloxy)-amino]-ethoxyimino}-2-[2-(trityl-amino)-thiazol-4-yl]-acetylamino}-3-chloromethyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 4-methoxy-benzyl ester (182068-65-1)

Guidance literature:

Multi-step reaction with 9 steps

1: 99 percent / K₂CO₃ / dimethylsulfoxide / 3 h / Ambient temperature

2: 1.)H₂NNH₂*H₂O, 2.) HCl / 1.) MeOH, room temperature, 10 h, 2.) MeOH, room temperature, 1 h

3: 95 percent / Et₃N / tetrahydrofuran; H₂O / 1.5 h / Ambient temperature

4: 52 percent / NaH / dimethylformamide / 15 h / 0 - 10 °C

5: 85 percent / HCl / ethyl acetate / 10 h / 0 deg C - room temperature

6: 98 percent / Et₃N / CH₂Cl₂ / 1.5 h / 0 deg C - room temperature

7: 100 percent / H₂NNH₂*H₂O / methanol / 14 h / Ambient temperature

8: 78 percent / ethanol; CHCl₃ / 10 h / Ambient temperature

9: 1.) Et₂NH, 2,6-lutidine, 2.) POCl₃ / 1.) CH₂Cl₂, -30 deg C, 0.5 h, 2.) CH₂Cl₂, -30 deg C - (-15) deg C, 4 h

With 2,6-dimethylpyridine; hydrogenchloride; sodium hydride; potassium carbonate; hydrazine hydrate; diethylamine; triethylamine; trichlorophosphate; In tetrahydrofuran; methanol; ethanol; dichloromethane; chloroform; water; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1016/0960-894X(96)00381-2

Reference yield:

O-(4-methoxybenzyl)-hydroxylamine HCl → (6R,7R)-7-{2-{(Z)-2-[Acetyl-(4-methoxy-benzyloxy)-amino]-ethoxyimino}-2-[2-(trityl-amino)-thiazol-4-yl]-acetylamino}-3-chloromethyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 4-methoxy-benzyl ester (182068-65-1)

Guidance literature:

Multi-step reaction with 7 steps

1: 95 percent / Et₃N / tetrahydrofuran; H₂O / 1.5 h / Ambient temperature

2: 52 percent / NaH / dimethylformamide / 15 h / 0 - 10 °C

3: 85 percent / HCl / ethyl acetate / 10 h / 0 deg C - room temperature

4: 98 percent / Et₃N / CH₂Cl₂ / 1.5 h / 0 deg C - room temperature

5: 100 percent / H₂NNH₂*H₂O / methanol / 14 h / Ambient temperature

6: 78 percent / ethanol; CHCl₃ / 10 h / Ambient temperature

7: 1.) Et₂NH, 2,6-lutidine, 2.) POCl₃ / 1.) CH₂Cl₂, -30 deg C, 0.5 h, 2.) CH₂Cl₂, -30 deg C - (-15) deg C, 4 h

With 2,6-dimethylpyridine; hydrogenchloride; sodium hydride; hydrazine hydrate; diethylamine; triethylamine; trichlorophosphate; In tetrahydrofuran; methanol; ethanol; dichloromethane; chloroform; water; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1016/0960-894X(96)00381-2

upstream raw materials:

4-methoxybenzyl-7-amino-3-chloromethyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate hydrochloride

(Z)-3-acetyl-1-(4-methoxyphenyl)-8-(2-(tritylamino)thiazol-4-yl)-2,6-dioxa-3,7-diazanon-7-en-9-oic acid

N-(4-methoxybenzyloxy)phthalimide

p-methoxybenzyl chloride

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